Iodine → HCID 68452317, compound

Temperature

-78 °C

To a stirred solution of diisopropylamine (3.09 mL, 21.8 mmol) in THF (60 mL) under at 0° C. was added n-butyllithium (6.83 mL, 20.0 mmol) dropwise over 5 min. After 10 min, the reaction mixture was cooled to −78° C., and a solution of (4-chloro-2-fluorobenzyloxy)(tert-butyl)dimethylsilane (5.00 g, 18.2 mmol) in THF (15 mL) was added slowly over 5 min. After 2 h at −78° C., a solution of iodine (5.54 g, 21.8 mmol) in THF (25 mL) was added over 10 min. After a further 20 min at −78° C., the reaction mixture was warmed to RT and was quenched with sodium thiosulfate, followed by water (100 mL). The separated aqueous solution was extracted with diethyl ether (2×60 mL). The combined organic phases were washed with saturated aqueous solution of sodium bicarbonate, and brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel (dichloromethane: hexane=10:90) gave (4-chloro-2-fluoro-3-iodobenzyloxy)(tert-butyl)dimethylsilane as colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.30 (1H, t, J=7.5 Hz), 7.17 (1H, d, J=7.1 Hz), 4.65 (2H, s), 0.75-0.85 (9H, m), 0.01 (6 H, s)

1. waitAfter 2 h at −78° C.
2. waitAfter a further 20 min at −78° C.
3. temperaturethe reaction mixture was warmed to RT
4. customwas quenched with sodium thiosulfate
5. extractionThe separated aqueous solution was extracted with diethyl ether (2×60 mL)
6. washThe combined organic phases were washed with saturated aqueous solution of sodium bicarbonate, and brine
7. dry with materialThe resulting organic solution was then dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-b3fb5f673d1e40c18e5671a531ba7b74

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759337B2